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Transition Metal‐Catalyzed Synthesis of Novel Biologically Relevant Tryptophan Analogues
Author(s) -
van Esseveldt Bart C. J.,
van Delft Floris L.,
Smits Jan M. M.,
de Gelder René,
Schoemaker Hans E.,
Rutjes Floris P. J. T.
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404012
Subject(s) - chemistry , benzofuran , sonogashira coupling , enantiopure drug , acetylene , indole test , tryptophan , combinatorial chemistry , catalysis , amino acid , transition metal , palladium , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry
A synthetic approach to the synthesis of novel tryptophan derivatives and benzofuran‐containing amino acids is detailed. The sequence starts from enzymatically resolved enantiopure acetylene‐containing amino acids, of which the acetylene function can be efficiently transformed into the targeted 2‐substited indole and benzofuran moieties via Sonogashira‐type coupling and metal‐catalyzed cyclization.